Bromomethyl 2-methoxyphenyl ketone → 4-(2-Methoxy-phenyl)-thiazol-2-ylamine

HRID 533962Notes

Reaction equation

HRID 533962 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][CH3:12])=O.[NH2:13][C:14]([NH2:16])=[S:15]>C(O)C>[CH3:12][O:11][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[C:3]1[N:13]=[C:14]([NH2:16])[S:15][CH:2]=1

Participants

4

Reactant 2

HCID 123440Bromomethyl 2-methoxyphenyl ketoneHCID 2723790Thiourea

Product 1

HCID 7352524-(2-Methoxy-phenyl)-thiazol-2-ylamineYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Bromo-1-(2-methoxy-phenyl)-ethanone (0.6388 g, 2.789 mmol) and thiourea (0.2289 g, 3.007 mmol) were dissolved in a 20 mL of ethanol. The reaction mixture was allowed to stir overnight at room temperature. The ethanol was evaporated to dryness and the crude product was dissolved in a minimum of dichloromethane. The crude product was then extracted twice with 1M sodium hydroxide and once with a saturated aqueous solution of sodium chloride. The organic layer was then dried over sodium sulfate, filtered, and evaporated to dryness to yield the pure product (0.529 g, 2.56 mmol, 92.0%). ESI-MS m/z calc. 206.3. found 207.1 (M+1)+ Retention time 1.86 minutes. 1H NMR (400 MHz, CD3CN) δ 3.91 (s, 3H), 5.54 (s, 2H), 6.97-7.02 (m, 1H), 7.03-7.06 (m, 1H), 7.23 (s, 1H), 7.24-7.29 (m, 1H), 8.06 (dd, J=7.8, 1.8 Hz, 1H).

Workup

  1. customThe ethanol was evaporated to dryness
  2. dissolutionthe crude product was dissolved in a minimum of dichloromethane
  3. extractionThe crude product was then extracted twice with 1M sodium hydroxide and once with a saturated aqueous solution of sodium chloride
  4. dry with materialThe organic layer was then dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-1adb2515537a4434be180769c653fb86
Source dataset
uspto-grants-2014_10
Patent number
US08853415B2

Reaction notes

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